Jay Rudman has long been described as a serial self-starter. His first entrepreneurial endeavor came as a young boy, selling Christmas wreaths for Junior Achievement. Three decades later, his endeavors have resulted in an array of successful business ventures making the Catapult team thrilled to have him in the position of Entrepreneur in Residence.
Rudman is an entrepreneur whose passion lies in helping businesses scale by focusing on strategy, sales, marketing and business development. Having successfully founded, operated, and sold three businesses, his talent for transitioning start-up ideas into viable business ventures makes him a sought-after EIR in the Chicago area.

Perhaps part of Rudman’s appeal is his approachableness, humility, and entrepreneurial wisdom curated from a long lineage of family owned businesses (he co-founded Paperly, with his wife Cindy). During our interview, Rudman emphasized the importance of continuously articulating the vision for your company and not being afraid to reach out to fellow entrepreneurs who have, more often than not, experienced similar challenges.

In his spare time, Rudman enjoys playing soccer, training for triathlons, coaching his kids' sports teams and doing most anything with his family.

Could you describe your first entrepreneurial experience?

Well actually, I didn't know you weren't supposed to NOT start your own business. My father, my step-father and my father-in-law all started and ran their own businesses, so I just assumed that's what you did when you grew-up. My first entrepreneurial experience was selling Christmas wreaths as part of Junior Achievement. I loved the fact that someone was willing to pay for our creation!

You’ve founded several companies yourself. How did these ideas come about?

Generally, these ideas are generated just from going out into the marketplace and talking to potential customers— Paperly, came about this way. My wife and I knew we had to figure out a way to tap into that demand. We explored a variety of different business models, and basically tripped upon the direct business model. Plus, in the current day and age, social media has been a large part of what’s allowed Paperly and other young organizations to explode into their respective industries.

Reflecting upon your own start-up experience, could you give us some insight into what it takes to be a successful entrepreneur?

The passion for what you do as well as the dream of being successful. In the start-up world, it’s normal to hit a lot of lows – each day is a constant rollercoaster. Every time you have a high, there’s always another challenge or obstacle around the corner. You really have to relish the highs and at times, almost ignore the lows. At the end of the day, it’s important to have an even keel, an appreciation about where you’re headed, and to enjoy the journey along the way.

It’s also important to constantly solicit feedback from colleagues and mentors. Sometimes you listen to people talk about their business struggles, and it just seems so apparent as to what they should do because you’ve been through the same struggle, but they haven’t yet. I’ve learned that you never provide direct advice. The best way to offer a suggestion is to say, “I’ve experienced that before, and this is what I’ve done” and then all you can hope is that they’ll see your example as analogous to what they’re experiencing. Maybe they’ll interpret it a little differently based upon whatever lens they’re looking through, but either way, it’s important to share what you know and let them interpret it as they will.

What do you think is the greatest challenge within the entrepreneurial world?

I’d say that the hardest challenges are usually people based— not so much with revenues, expenses, or investors. Instead, it’s really about the team and building a strong culture. It’s easy to get infatuated with your own product and to lose sight of what it is that the customer truly wants. You also have this same challenge with communication— just because you know the end goal and value of your product, doesn’t mean that everyone else knows it too. When you have new team members, or perhaps when a team member steps astray for a moment, it’s that culture of communication that really keeps it all anchored together.

I’ve also found, that you have to clearly articulate the vision as to where your business is heading. Even if it’s all clearly articulated in your own mind, your team members need to be able to rally around the goal that you’re driving for, and not just the goals you have on a daily basis. Every day, it’s important to get excited about what the overall future holds for the team.

What exactly attracted to you Catapult?

Well I’ve found that there are two different types of people in the start-up world—you’re either a start–up entrepreneur or a manager. I absolutely prefer the start-up position, which is what’s so invigorating about Catapult. I’ve already done a lot of entrepreneurial mentoring and am always excited at the opportunity to share experiences with organizations that are above and beyond just an idea. One thing I really enjoy about the start-up community is commiserating with others who can appreciate the ups and downs within our respective journeys. From what I can tell so far, the Catapult companies already have great traction and post-revenue opportunities. These companies are right at the precipice of the true acceleration scale of their businesses. With an injection of experience and luck, hopefully everything will work out!